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Step 1
Choose any sad image of your choice and edit the size to 19 by 19 pixels with a photo-editing application. You can easily download sad faces, or get creative and create your own sad image. Any image will work, as long as it is the right size. Once you have edited the size, save the image in a location that you can easily find later.
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Step 2
Open the main window of MSN Messenger and click "Tools," then "My Emoticons," then "Create" and then "Find Image."
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Step 3
Navigate to where you saved your image and select the file. Once it is open, you will be asked to type a keyboard shortcut that you will use as a command to send your new emoticon. Type whatever you like--something you will remember, such as "!sad:("--and click "OK."
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Step 4
Start a new chat window and type your keyboard shortcut into the message window. Send your message, and you will see your fantastic sad emoticon in the chat screen.
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Step 5
Teach your friends how to create new emoticons, and trade them with one another.







